DIOSMETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O6
Molecular Weight	300.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COc1ccc(cc1O)-c2cc(=O)c3c(cc(cc3o2)O)O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N

InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H12O6
Molecular Weight	300.2635
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27725131 | https://www.ncbi.nlm.nih.gov/pubmed/28835383 | https://www.ncbi.nlm.nih.gov/pubmed/24092244

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A1 29 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 7728	140.0 nM [IC50]
Cytochrome P450 1A2 65 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 7728	2.4 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 7728	29.0 nM [IC50]
Estrogen receptor beta 106 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383	Agonist 2470
NF-kappa B signaling pathway 77 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238	Inhibitor 7728

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383	Primary	Preclinical	Unknown Approved Use Unknown
Hepatocellular carcinoma 78 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238	Preventing	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27725131	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Resistance of MCF-7 cells to dimethylbenz(a)anthracene-induced apoptosis is due to reduced CYP1A1 expression.	2002 Aug	12118336
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.	2002 Oct	12150856
DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells.	2003 Feb 24	12592376
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.	2003 Sep 9	12972054
Antitubercular constituents of Valeriana laxiflora.	2004 Jun	15229801
Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.	2004 Nov 15	15476679
Analysis and quantification of flavonoidic compounds from Portuguese olive (Olea europaea L.) leaf cultivars.	2005 Feb	15715265
Complete assignments of NMR data of 13 hydroxymethoxyflavones.	2007 Dec	17987643
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.	2007 Feb	17108059
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.	2008 Apr	18186104
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.	2008 Apr 1	18249545
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.	2008 Aug 15	18590707
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.	2008 Jun	18269307
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.	2008 Mar 15	18191104
A new ferulic acid ester and other constituents from Dracocephalum peregrinum.	2008 Oct	18958424
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.	2009 Feb	19254799
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009 Feb	19014974
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.	2009 Feb 8	18976853
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.	2009 Jan 8	19133145
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.	2009 Jul	19590707
Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.	2009 Jun	19424633
Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?	2009 Mar 16	19010313
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.	2009 Mar 25	18835421
[Chemical constituents of Galium verum].	2009 Nov	20209910
[Studies on flavones from Flos Chrysanthemi Indici].	2009 Oct	20112712
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.	2009 Sep	20183323
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.	2010	20877134
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.	2010 Jun	22110336
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.	2010 Mar 2	20479987
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.	2015 Mar	25388478

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50mg /kg/every other day for 6 weeks

Route of Administration: Intraperitoneal

In Vitro Use Guide

Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 08:24:59 UTC 2021` Edited by `admin` on `Sat Jun 26 08:24:59 UTC 2021`
Record UNII	TWZ37241OT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIOSMETIN

Official Name

English

4'-METHYLLUTEOLIN

Common Name

English

DIOSMETIN [WHO-DD]

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-

Systematic Name

English

3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE

Systematic Name

English

DIOSMETIN [INCI]

Common Name

English

DIOSMETIN [MI]

Common Name

English

5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

DIOSMETINE

Common Name

English

LUTEOLIN-4'-METHYL ETHER

Common Name

English

CYANIDENON-4'-METHYL ETHER 1479

Common Name

English

DIOSMETOL

Common Name

English

5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-

Systematic Name

English

Classification Tree Code System Code

DSLD

4156 (Number of products:7)